


daddy's matching set

by hey_you_with_the_face



Series: Kinky SPN Bingo 2017 [3]
Category: Supernatural
Genre: Alternate Universe - Angels & Demons, Anal Fingering, Anal Sex, Angel Castiel (Supernatural), Angel Jimmy, Consort Castiel, Consort Jimmy, D/s elements, Daddy Kink, Knight of Hell Dean Winchester, M/M, Making Out, Twincest
Language: English
Status: Completed
Published: 2017-06-23
Updated: 2017-06-23
Packaged: 2018-11-18 00:16:25
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,639
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/11279766
Author URL: https://archiveofourown.org/users/hey_you_with_the_face/pseuds/hey_you_with_the_face
Summary: Helping Crowley consolidate power in Hell had been fun but being in charge of punishing rogue demons...not so much; luckily Dean has his angels to entertain him...





	daddy's matching set

**Author's Note:**

> Another square filled for my kink bingo :)  
> This time it was 'daddy kink'

Being the co-ruler of Hell was a very boring job.

When Dean had first been approached by Crowley about a master plan to consolidate the aimless mass of demons that made up the underworld into something more concrete, he’d been intrigued enough to accept. It had been hard to turn down the offer when Crowley had mentioned his plan would capitalize on Dean’s most valued traits.

His exceptional skills concerning violence and his aptitude for killing.

As a knight of Hell, it would have been easy for Dean to swoop in and claim the crown for himself but to be completely honest, the idea of ruling the multitudes of sad sacks that made up demonkind nowadays sounded as fun as jerking off with sandpaper. So, with this in mind, Dean watched Crowley assume the throne; he would have been completely content to disappear into obscurity but apparently Crowley had another proposition for him.

Rule by his side and use his considerable talents to help keep the subjects in line.

Now Dean’s job was to listen to whining maggots beg for mercy and light sentences while he sat in his very own throne room that Crowley insisted he have. Sometimes he’d have to go to the actual throne room for public executions but other than that, Dean kept to his wing of the palace and dealt with the traitors brought before him.

It had already been a long day at this point and Dean was starting to find himself losing interest. His lack of interest wasn’t helped by the utter shit standing in front of him, a demon who’d foolishly thought he could just walk out of Hell. The sound of the demon’s pleading voice was starting to grate on his nerves and in an attempt to block him out, Dean glanced to the side of his throne; what he saw there immediately put him in a better mood.

But then, seeing his angels always did. 

Dean could still remember the day he received his angels, Castiel and Jimmy. They had gotten cut off from their garrison during a skirmish and stumbled into Dean’s path. He had been struck dumb by their perfectly matching features and pristine wings and in that moment he knew he needed to have them; which is why when Crowley asked what spoils he wanted from the battle, Dean hadn’t hesitated to claim them. 

It had taken a while for his angels to get used to him but they quickly learned that, since going back to Heaven wasn’t going to happen and Dean sometimes suspected they didn’t really miss it, being with Dean was the best option. It also helped that he spoiled his angels rotten. 

They’re only purpose in life was to entertain Dean and not only were they extremely talented at this task, they thoroughly enjoyed it. 

As Dean looked over to distract himself from the walking talking puke stain that was currently trying to win his clemency, he saw that Castiel was picking lightly at his brother’s wings while Jimmy napped lightly on the large pillow nest Dean had set up for them. The incessant whining faded blissfully into the background as his gaze greedily observed his angels.

Watching Castiel’s hands caress the sensitive feathers of Jimmy’s brilliantly white wings as he carefully groomed him had Dean’s mind swiftly turning to more important matters. Namely how much he wanted them. 

All he could think about was watching his angels kissing each other; Dean figured he’d have them start out slow, with soft kisses and barely there touches that were entirely too innocent as a starting point for where Dean planned to lead them. Not that they would mind but then Dean had always suspected his pristine twin angels were absolutely filthy just under the surface even before he’d even met them considering how eagerly they took to their new lot in life. 

Dean shifted on his throne as he imagined the twins getting rougher with each other, maybe by his orders but also because they just couldn’t help it. Castiel would start tugging on Jimmy’s hair, causing him to groan while Jimmy, always the little shit, would shove a hand down his twin’s underwear in retaliation.

Mmmm...yeah, that was nice; much nicer than his current situation by far.

Just then, Jimmy stirred; he rose up and rubbed at his eyes sleepily and pulled Cas down to him. Dean’s breath caught slightly as the beginning of his fantasy started taking place right before his eyes; sure it was in reverse since Jimmy was taking the lead but who really gave a fuck?

And speaking of giving a fuck…

“Everybody out,” he ordered sharply, not bothering to look away from his angels as they rolled around on the plush cushions.

“But my lord, there are still several cases that need to be heard today,” one of the various henchmen Dean never really had time to notice whined, “The King will not be please---”

Dean rolled his eyes and turned to level an annoyed glare at him. “Crowley can suck my dick,” he replied without concern before pointing towards the door to his throne room. “You can tell him I told you that; I’m done for the day so all of you get the fuck out of my throne room.”

Sounds of scurrying feet and hurried movements echoed through the room as the accused, the guards and other attendants ran for the door; knowing Dean’s temperament as they did, none of them wanted to be the last in the room. Finally the door shut with a mighty thud.

Alone at last.

While Dean didn’t mind the court seeing his angels lounging about in the lingerie that he’d picked out especially for them on his trips topside, no one got to see them all pretty and flushed.

Settling himself more comfortably on his throne, legs sprawling out wide, Dean caught Cas’ eye and crooked a finger at him. Cas grinned and nodded, grabbing Jimmy by the arm and pulling him along; Jimmy made a sound of protest but once saw where they were going, he beamed. 

“Yes, daddy?” Jimmy purred as they stood before him. Dean rolled his eyes at the title; it was something that his mischievous little angel had started ages ago as a joke but at some point along the way, it had stopped being a joke. Jimmy really got off on calling him daddy so Dean indulged him.

And no one had to know that every time that word slipped from the those plush lips Dean felt a spark of heat in his gut.

Dean grabbed them by the hand and pulled them in so they were each straddling one of his muscular denim clad thighs. “Were you two having fun over there?” he asked, smirking as Cas blushed since he was always a little embarrassed when he and Jimmy got carried away in front of the court. “‘Cause it sure looked like you were.”

“Not as much fun as we do with you,” Jimmy replied with a coy smile. He sat down lightly on Dean’s thigh and started rubbing a hand up and down the t-shirt covering his chest, his face formed into an exaggerated pout. “You haven’t been playing with us lately, daddy.”

Cas mirrored his twin’s position and nodded. “You’ve been so busy with the court that we’ve had to entertain ourselves,” he added as he leaned down onto Dean’s side. “Fucking isn’t nearly as satisfying without you.”

So it was going to be like that was it.

Dean could play this game.

Nodding sympathetically, Dean caressed Jimmy’s thigh with one hand and Cas’ hip with the other; his fingers toyed with the hems of the panties. Today they were wearing matching ice blue lace numbers that cupped them softly; they were only one pair of many but he knew from experience that these lovely pairs of panties were going to be ruined so he took a moment to enjoy the way they complimented the twins’ pale skin.

“You’re very right, baby,” he said, attempting to look contrite. Jimmy’s eyes were gleaming with excitement, probably trying to guess where Dean was going to go with this. Dean gave an obviously fake sigh of exhaustion that caused confusion to cross his face, “But daddy is still kind of tired; I’ll need a little bit of time to get the energy to play with my angels. Maybe you and Cas could give me a little show?”

Jimmy brightened again as he realized the game and he pulled insistently on Cas’ arm so he was sitting upright; they leaned towards each other and Cas started placing kisses down his twin’s neck while Jimmy ran his hands up and down his sides. Dean leaned back, lacing his fingers behind his head as he did, and enjoyed the show.

And what a damn fine show it was.

The angle was a bit awkward since they were both in his lap but his angels made it work; soon they began kissing each other, soft kisses that slowly transformed into a deep and sensual makeout complete with wandering hands. As usual, Jimmy’s hands dipped down into Cas’ panties first; he never could resist teasing him, though Cas was quick to follow. Soon they were rocking into each other hands as much as they could in their current position; their mouths parting to form small o’s of pleasure. As time went on, Dean was more than pleased to see that their hips were rocking down onto his thighs, trying to get more friction on their panty clad cocks.

The sight of his sweet angels driving each other higher and higher had his own dick straining against his jeans; it seemed like such a shame to interrupt Cas and Jimmy at this point so, without stopping them, he undid his belt and pants to pull himself out of his underwear. Dean sighed contentedly as he stroked his hardened length leisurely; He had no intention of getting off on his own; this was just to keep his arousal at a comfortable level as he enjoyed the soft moans and wet sounds of Cas and Jimmy making out in his lap.

“Mmmm...daddy, can we play with you now?” Jimmy moaned as he parted his mouth from Cas’. He was looking down greedily at where Dean’s hand slid over his cock. Cas occupied himself with nipping and sucking at Jimmy’s neck but Dean could see him watching him out of the corner of his eye, curious about what his answer would be.

Pretending to ponder this question as if he wasn’t about ready to crack, Dean hummed contemplatively as he continued to jerk off slowly. “Hmmm, I’m not sure,” he said with mock indecision. “I might need some more time.”

“Please, daddy,” Jimmy said, looking at him with those big blue eyes. “Please, can we have some fun? Today has been so boring.”

Cas, abandoning his post at his twin’s neck, joined in with a pleading, “Yes, please, sir.”

Dean shivered pleasantly as his angels turned on the charm. Not that it was needed, they knew he couldn’t say no to them under normal circumstances; there was no way he could say no to them all flushed and eager to please him.

“Alright,” he said, acting as he weren’t already aching to have their mouths working on him. Dean nudged them off his legs and, with a playful swat on each of their asses, sent them towards the bedroom 

He may have taken a moment to savor the swing of their lace covered hips between their wings as they scurried to do as he told them. The view made his dick throb as Dean imagined what awaited him in their room.

Deciding he’d wasted enough time, Dean tucked himself away and strode towards the large doors that led to the bedroom, his heavy boots echoing in the empty throne room; the twins had left it ajar in their rush so he only had to push it lightly to walk inside. Shivers of anticipation skated over his skin as he walked in to see Cas and Jimmy sprawled on the bed, kissing languidly and running their fingers through each other’s feathers.

It was one of the most fucking perfect things Dean had ever seen.

Dean walked to the end of the bed, he stripped off his shirt, making sure to flex a bit for his angels’ benefit before sliding his pants off and kicking off his boots; his cock, still half hard, bobbed lazily as it was freed from his underwear. Once he was completely bare, he crawled on to the bed; the twins looked at him eagerly, both wanting to be the one Dean fucked first.

He made his way over to Cas, shifting between his legs and swiftly pulling off his panties, much to Jimmy’s obvious disappointment. An open pout fell over his features but Dean knew how to fix that.

“Don’t worry, Jimmy,” Dean cooed, reaching to caress his face. “It’ll be your turn soon enough and if you’re a good boy and behave until after Cas’ turn; I’ll fuck you until I come in your ass, how’s that sound?”

This promise caused Jimmy to brighten considerably; he loved having Dean’s come in his ass. “Good, daddy, very fucking good,” he replied with a grin before looking at him with half lidded eyes. “What can I do to be a good boy?”

“Hmmm, what can you do for me?” Dean hummed thoughtfully, running a hand up and down Cas’ thigh; he could tell that him being between his legs but not doing anything was driving Cas nuts so he may have pretended to think a bit longer after he’d decided. “I know, I think I’d you to finger yourself for me; how does that sound?”

Jimmy nodded and immediately rolled onto his back; both Dean and Cas watched raptly as Jimmy slowly and smoothly slid off his lacy panties off his hips, down his thighs and over his feet; his impish angel always liked to show-off and Dean suspected he was an exhibitionist at heart. A hand reached between his legs to ease out the plug that Dean had put in him that morning; memory jogged by this, Dean slid a hand down and started playing with Cas’ plug, pulling it out so he could place the tip of himself to his prepared entrance. He waited until he heard the soft gasp of Jimmy breaching himself with his fingers before pushing forward slowly but firmly. 

The shuddery cry that Cas let out at being finally filled resonated beautifully with the resulting moan from Jimmy at seeing his twin being fucked, if Dean said so himself.

After a second to savor the tight warmth encasing him, Dean hefted Cas’ leg up onto his hip and began skillfully thrusting him causing Cas to let out a deep groan. One hand reached up to grab at Dean’s bicep while the other shot out to the side to grab Jimmy’s shoulder. Heat raced up and down Dean’s spine in time with the forward pumping of his hips which only fueled the burning heat in his groin, a situation that wasn’t helped by the sight of Cas writhing underneath him. 

Cas was making every sinful noise in the book as Dean fucked into him hard and fast; Dean’s favorite had to be the broken moans he pulled out of him every time his cock brushed his prostate, a close second would be the surprised gasp that Jimmy caused when he reached over and started toying with his twin’s nipples. Through the haze of lust and sex clouding Dean’s mind, he noticed that Jimmy still had a hand working between his legs and the thought of him trying so hard to please him just added to Dean’s euphoric mood.

He pulled his gaze away from Jimmy and looked down when the grip on his bicep tightened. What he saw confirmed his suspicions; Cas was holding on to the edge for dear life, waiting for Dean to give him permission. His eyes were squeezed shut and his mouth was open as he groaned with every twist of Dean’s hips.

“Is there something you need Cas?” Dean panted, speeding up his thrusts and chuckling as Cas keened loudly, biting his lip. “All you have to do is ask.”

Blue eyes gazed up at him, desperation evident in every corner of them.

It was beautiful.

“Please, sir, please,” he begged brokenly between gasps and moans. Dean felt his fingers dig into his bicep in a desperate bid to hold back the tide of his orgasm. “Can I come? Please?”

Then, to his surprise, Jimmy joined in.

“Make him come, daddy,” Jimmy moaned, his eyes fixed hungrily on where Dean and Cas’ hips were moving together. “Do it, please.”

Dean pretended to think it over for a few seconds, a few seconds that appeared to drive Cas almost to the breaking point, before nodding. He turned to Jimmy and grinned, “Touch him, Jimmy. Make him come for us.”

Jimmy’s hand shot out lightning fast and he grasped Cas’ leaking cock in his hand. His twin cried out and bucked into his fist and Jimmy smiled. “That’s it, Cas; fuck my fist, fuck my fist and come for us.”

Dean shuddered himself at Jimmy’s words and it took everything he had not to let go as Cas tensed and then fell apart beneath him with a shout, moaning their names as he did, streaking his stomach and chest with white.

The erratic pulsing of Cas’ ass around him almost tipped Dean over the edge; he was forced to bite his lip and clutch at the base of his cock to stave off coming. His skin was on fire and his body screamed at him to keep going, to rut into Cas just a few more times, but he resisted.

He had a promise to keep. 

He pulled out gingerly once Cas allowed his legs to unwrap themselves from Dean’s waist; Dean felt a wave of pride break through the mind melting lust in his brain at the sight of Cas being so fucking blissed out. A pitiful whine broke him out of his reverie.

“Daddy,” Jimmy whined petulantly, looking at Dean longingly. “I’ve been good, it’s my turn now.”

Dean leaned down and gave Cas a slow kiss, murmuring a few praises that had him smiling lazily, before suddenly lunging over at Jimmy.

He caught a glimpse of surprised blue eyes right before they slammed shut as he knocked Jimmy’s hand aside and slid home swiftly. Jimmy groaned, his hands reaching up to scrabble at Dean’s shoulders in response to the sudden assault.

“Always so impatient, Jimmy,” Dean grunted with every rough thrust. Repeated, shuddering whines spilled out of Jimmy as he worked his hips up into Dean’s frantically. “Always pushing my buttons.” 

A particularly hard thrust had them both groaning. The pulsing heat in Dean’s belly was quickly reaching the point of no return so he pushed on the back of Jimmy’s thighs, almost bending him in half in an effort to get deeper. Jimmy keened loudly, his fingernails scraping down his chest caused Dean’s entire body to flash with sparks of pleasure pain that shot right to his dick.

“I think---I think you do it on purpose,” Dean continued, changing his rhythm so he was moving in and out of Jimmy more slowly but harder; Jimmy’s keening whines to turned to deep debauched groans. “I think you like being held down and fucked like a dirty slut.” This earned him an even louder moan and Dean grinned. “Yes, that’s it; my angel is a filthy slut isn’t he?”

“Yes,” Jimmy practically sobbed, bucking his hips up to take Dean deeper. “I’m your dirty slut!”

Only sheer willpower kept Dean from blowing his load then and there. “Yeah, yeah you are,” he growled, ramming into him now; he was so fucking close he couldn’t take it anymore. “And dirty sluts do as they’re told so come for me, Jimmy; you come for me right fucking now.”

And he did.

Jimmy gasped, his entire body seizing up while his nails dug almost painfully into Dean’s sides, then he honest to god shrieked his name as he came violently between them without Dean having to to lay a hand on his cock. Dean wasn’t so much dragged over the edge behind him after witnessing this so much as he was shot over it like a fucking cannon ball. He drove himself deep inside Jimmy’s ass, a rumbling groan bursting out of him, as his orgasm hit him like a wave of liquid fire and he emptied himself into him.

Just as promised.

They collapsed in a sweaty pile of limbs and Dean rolled over onto his back. He glanced over to see Cas watching them, a content smile on his face, and shimmied back so he was resting against the pillows. Jimmy grumbled in irritation when Dean pulled on his arm to bring his limp, exhausted body next to him while Cas crawled eagerly across the small space to take his place at Dean’s other side. His angels shuffled around a bit, settling in comfortably with their heads on his chest and his arms around their bare shoulders until they could fan their wings out, their feathers criss crossing over him protectively.

Dean smiled and bent his head to kiss them on the tops of their sex mussed hair; they were already passed out from their recent exertion, the light puffs of their breath ghosting across his sweat damp skin. 

At the end of the day, no matter how rough things got, Castiel and Jimmy were his perfect matching angels and Dean didn’t know what he’d do without them.

**Author's Note:**

> I'll tell you what, I can't seem to fight the fluff; I set out to write a filthy daddy kink one-shot and I still end up a sweet fluffy ending, haha


End file.
